Basic bisazo compounds
View Patent ↗The invention relates to basic bisazo compounds according to formula (I) wherein all substituents are defined as in Claim 1 , their production, their use as dyestuffs as well as material dyed with these dyestuffs.
1. A compound of formula (I)
where
R 0 is a substituted or an unsubstituted C 1 to C 4 alkyl group,
R 1 is selected from the group consisting of: H, N(R 7′ R 7″ ), a substituted C 1 to C 4 alkyl group, an unsubstituted C 1 to C 4 alkyl group, and CN,
R 2 or R 2′ are selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, an unsubstituted C 1 to C 4 alkyl group, and a group with the formula
[(CR 8 R 8′ )—(CR 9 R 9′ ) m —(CR 10 R 10′ ) n —(CR 11 R 11′ ) o ]—NR 12 R 12′
wherein
m, n and o are 1 or 0,
R 8 , R 8′ , R 9 , R 9′ , R 10 , R 10′ , R 11 or R 11′ are independently selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, and or an unsubstituted C 1 to C 4 alkyl group;
and R 12 or R 12′ are independently selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, and an unsubstituted C 1 to C 4 alkyl group,
R 3 is selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, an unsubstituted C 1 to C 4 alkyl group, a substituted C 1 to C 4 alkoxy group, and an unsubstituted C 1 to C 4 alkoxy group,
R 4 is selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, an unsubstituted C 1 to C 4 alkyl group, a substituted C 1 to C 4 alkoxy group, and an unsubstituted C 1 to C 4 alkoxy group,
R 5 is selected from the group consisting of: H, substituted C 1 to C 9 alkyl group, and an unsubstituted C 1 to C 9 alkyl group, wherein the C 1 to C 9 alkyl group is a branched or linear C 1 to C 9 alkyl group,
R 6 is selected from the group consisting of: a substituted C 1 to C 9 alkyl group, an unsubstituted C 1 to C 9 alkyl group, an unsubstituted aryl group, and a substituted aryl group, wherein the C 1 to C 9 alkyl group is a branched or linear C 1 to C 9 alkyl group,
wherein the sum of carbon atoms of R 5 and R 6 is at least 4 carbon atoms,
R 7′ or R 7″ are independently selected from the group consisting of: a substituted C 1 to C 4 alkyl group, an unsubstituted C 1 to C 4 alkyl group, and R 7′ and R 7″ form together with the nitrogen atom a five or six membered aromatic or a five or six membered cyclo alipahatic, wherein the five or six membered rings are substituted by a C 1 to C 4 alkyl group or the five or six membered rings are not further substituted.
2. A compound according to claim 1 , wherein
R 0 is a substituted C 1 to C 4 alkyl group or an unsubstituted C 1 to C 4 alkyl group,
R 1 is selected from the group consisting of: N(R 7′ R 7″ ), a substituted C 1 to C 4 alkyl group, and an unsubstituted C 1 to C 4 alkyl group,
R 2 or R 2′ is a group with the formula
[(CR 8 R 8′ )—(CR 9 R 9′ ) m —(CR 10 R 10′ ) n —(CR 11 R 11′ ) o ]—NR 12 R 12′
wherein m, n and o are 1 or 0, and R 8 , R 8′ , R 9 , R 9′ , R 10 , R 10′ , R 11 or R 11′ are independently selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, and an unsubstituted C 1 to C 4 alkyl group; and
R 12 or R 12′ are independently selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, and an unsubstituted C 1 to C 4 alkyl group,
R 3 is selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, an unsubstituted C 1 to C 4 alkyl group, a substituted C 1 to C 4 alkoxy group, and an unsubstituted C 1 to C 4 alkoxy group,
R 4 is selected from the group consisting of: H, C 1 to C 4 alkyl group, and C 1 to C 4 alkoxy group
R 5 is selected from the group consisting of: H, substituted C 1 to C 9 alkyl group, and an unsubstituted C 1 to C 9 alkyl group, wherein the C 1 to C 9 alkyl group is a branched or linear C 1 to C 9 alkyl group,
R 6 is selected from the group consisting of: a substituted C 1 to C 9 alkyl group, an unsubstituted C 1 to C 9 alkyl group, an unsubstituted aryl group, and a substituted aryl group, wherein the C 1 to C 9 alkyl group is a branched or linear C 1 to C 9 alkyl group,
wherein the sum of carbon atoms of R 5 and R 6 is at least 4 carbon atoms,
R 7′ and R 7″ form together with the nitrogen atom a five or six membered aromatic, wherein the five or six membered rings is substituted by a C 1 to C 4 alkyl group or the five or six membered ring is not further substituted.
3. A compound according to claim 2 , wherein R 1 is
wherein the * shows the point of attachment to the rest of the molecule and wherein
R 13 is selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, an unsubstituted C 1 to C 4 alkyl group, a substituted C 1 to C 4 alkoxy group, and an unsubstituted C 1 to C 4 alkoxy group.
4. A compound according to claim 3 wherein
R 2 or R 2′ is a group with the formula
—[(CR 8 R 8′ )—(CR 9 R 9′ )—(CR 10 R 10′ )]—NR 12 R 12′
wherein
R 8 , R 8′ , R 9 , R 9′ , R 10 or R 10′ are independently selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, and an unsubstituted C 1 to C 4 alkyl group; and
R 12 or R 12′ are independently selected from the group consisting of: H, a substituted C 1 to C 4 alkyl group, and an unsubstituted C 1 to C 4 alkyl group.
5. A compound of formula (5):
6. A compound according to claim 1 , wherein R 6 is an unsubstituted or substituted aryl group.
7. A compound according to claim 6 , wherein R 5 is H.
8. A compound according to claim 1 , wherein the sum of carbon atoms of R 5 and R 6 together is at least 5.
9. A compound according to claim 1 , wherein the sum of carbon atoms of R 5 and R 6 together is 5, 6, 7, 8, or 9.
10. A compound according to claim 1 , wherein one or more of R 5 and R 6 is a substituted or unsubstituted C 1 -C 9 alkyl group, wherein the C 1 to C 9 alkyl group is a branched or linear C 1 to C 9 alkyl group.
11. A compound according to claim 10 , wherein R 5 is H.
12. A compound according to claim 1 , wherein R 5 is H.
13. A liquid dyeing preparation or ink jet ink comprising at least one compound of formula (I) according to claim 1 .
14. A compound of one of the following formulas: